Sodium Hydroxide → HCID 58223409, compound

HRID 41269Notes

Reaction equation

HRID 41269 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:14]=[C:13]([CH2:15][O:16][CH3:17])[CH:12]=[C:11]([O:18][CH3:19])[C:10]=1[C:20]1[N:21]2[N:27]=[C:26]([S:28]([CH3:31])(=O)=O)[CH:25]=[C:22]2[S:23][CH:24]=1.[OH-].[Na+]>[Ti](Cl)(Cl)(Cl)Cl.O1CCCC1>[CH3:7][O:8][C:9]1[CH:14]=[C:13]([CH2:15][O:16][CH3:17])[CH:12]=[C:11]([O:18][CH3:19])[C:10]=1[C:20]1[N:21]2[N:27]=[C:26]([S:28][CH3:31])[CH:25]=[C:22]2[S:23][CH:24]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 582234563-[2,6-Dimethoxy-4-(methoxymethyl)phenyl]-6-(methylsulfonyl)pyrazolo[5,1-b][1,3]thiazole

Product 1

HCID 58223409HCID 58223409, compoundYield 9.3%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To tetrahydrofuran (20 mL) was added dropwise titanium tetrachloride (1.10 mL, 10.1 mmol) at −78° C., and the mixture was stirred for 10 minutes. At the same temperature, a tetrahydrofuran (20 mL) solution of lithium aluminum hydride (767 mg, 20.1 mmol) was gradually added dropwise and stirred for 30 minutes. To the mixture was added 3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-6-(methylsulfonyl)pyrazolo[5,1-b][1,3]thiazole (384 mg, 1.01 mmol), and the mixture was stirred at room temperature for 30 minutes. The mixture was heated at 50° C. for one hour. After the reaction was completed, 5N sodium hydroxide was gradually added dropwise while cooling on ice to stop the reaction. The reaction mixture was filtered with Celite and extracted with ethyl acetate, the organic layer was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-heptane/ethyl acetate=1/1) to obtain the title compound (32.8 mg, 0.094 mmol).

Workup

  1. stirringstirred for 30 minutes
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. temperaturewhile cooling on ice
  4. customthe reaction
  5. filtrationThe reaction mixture was filtered with Celite
  6. extractionextracted with ethyl acetate
  7. dry with materialthe organic layer was dried over magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (n-heptane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-4c42e7d511d04b8e9cad177ae8f1ab23
Source dataset
uspto-grants-2013_09
Patent number
US08530504B2

Reaction notes

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